Disclosed herein are colorant compounds. More specifically, disclosed herein are colorant compounds particularly suitable for use in hot melt or phase change inks. One embodiment is directed to a compound comprising three or more moieties of the formula
wherein (A) each R1, independently of the others, is (i) an alkyl or alkylene group, (ii) an aryl or arylene group, (iii) an arylalkyl or arylalkylene group, (iv) an alkylaryl or alkylarylene group, (v) a silyl or silylene group, or (vi) a siloxy group, (B) each R2, independently of the others, is (i) an alkyl or alkylene group, (ii) an aryl or arylene group, (iii) an arylalkyl or arylalkylene group, (iv) an alkylaryl or alkylarylene group, (v) a silyl or silylene group, (vi) a siloxy group, or (vii) a group of the formula
wherein r and s are each, independently of the other, integers representing a number of repeat —CH2— groups, (C) each R3, independently of the others, is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, or (iv) an alkylaryl group, (D) each X, independently of the others, is (i) a direct bond, (ii) an oxygen atom, (iii) a sulfur atom, (iv) a group of the formula —NR40— wherein R40 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, or (v) a group of the formula —CR50R60— wherein R50 and R60 each, independently of the other, is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and (E) each Z, independently of the others, is (i) a hydrogen atom, (ii) a halogen atom, (iii) a nitro group, (iv) an alkyl group, (v) an aryl group, (vi) an arylalkyl group, (vii) an alkylaryl group, (viii) a group of the formula
wherein R70 is an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, a silyl group, or a siloxy group, (ix) a sulfonyl group of the formula —SO2R80 wherein R80 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, a silyl group, or a siloxy group, or (x) a phosphoryl group of the formula —PO3R90 wherein R90 is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, a silyl group, or a siloxy group; said moieties being bonded to a central atom, monomeric group of atoms, oligomer, or polymer. Another embodiment is directed to a phase change ink comprising a phase change ink carrier and a colorant compound comprising three or more moieties of the formula
said moieties being bonded to a central atom, monomeric group of atoms, oligomer, or polymer.
In general, phase change inks (sometimes referred to as “hot melt inks”) are in the solid phase at ambient temperature, but exist in the liquid phase at the elevated operating temperature of an ink jet printing device. At the jet operating temperature, droplets of liquid ink are ejected from the printing device and, when the ink droplets contact the surface of the recording substrate, either directly or via an intermediate heated transfer belt or drum, they quickly solidify to form a predetermined pattern of solidified ink drops. Phase change inks have also been used in other printing technologies, such as gravure printing, as disclosed in, for example, U.S. Pat. No. 5,496,879 and German Patent Publications DE 4205636AL and DE 4205713AL, the disclosures of each of which are totally incorporated herein by reference.
Phase change inks for color printing typically comprise a phase change ink carrier composition which is combined with a phase change ink compatible colorant. In a specific embodiment, a series of colored phase change inks can be formed by combining ink carrier compositions with compatible subtractive primary colorants. The subtractive primary colored phase change inks can comprise four component dyes, namely, cyan, magenta, yellow and black, although the inks are not limited to these four colors. These subtractive primary colored inks can be formed by using a single dye or a mixture of dyes. For example, magenta can be obtained by using a mixture of Solvent Red Dyes or a composite black can be obtained by mixing several dyes. U.S. Pat. No. 4,889,560, U.S. Pat. No. 4,889,761, and U.S. Pat. No. 5,372,852, the disclosures of each of which are totally incorporated herein by reference, teach that the subtractive primary colorants employed can comprise dyes from the classes of Color Index (C.I.) Solvent Dyes, Disperse Dyes, modified Acid and Direct Dyes, and Basic Dyes. The colorants can also include pigments, as disclosed in, for example, U.S. Pat. No. 5,221,335, the disclosure of which is totally incorporated herein by reference. U.S. Pat. No. 5,621,022, the disclosure of which is totally incorporated herein by reference, discloses the use of a specific class of polymeric dyes in phase change ink compositions.
Phase change inks have also been used for applications such as postal marking, industrial marking, and labelling.
Phase change inks are desirable for ink jet printers because they remain in a solid phase at room temperature during shipping, long term storage, and the like. In addition, the problems associated with nozzle clogging as a result of ink evaporation with liquid ink jet inks are largely eliminated, thereby improving the reliability of the ink jet printing. Further, in phase change ink jet printers wherein the ink droplets are applied directly onto the final recording substrate (for example, paper, transparency material, and the like), the droplets solidify immediately upon contact with the substrate, so that migration of ink along the printing medium is prevented and dot quality is improved.
Compositions suitable for use as phase change ink carrier compositions are known. Some representative examples of references disclosing such materials include U.S. Pat. Nos. 3,653,932, 4,390,369, 4,484,948, 4,684,956, 4,851,045, 4,889,560, 5,006,170, 5,151,120, 5,372,852, 5,496,879, European Patent Publication 0187352, European Patent Publication 0206286, German Patent Publication DE 4205636AL, German Patent Publication DE 4205713AL, and PCT Patent Application WO 94/04619, the disclosures of each of which are totally incorporated herein by reference. Suitable carrier materials can include paraffins, microcrystalline waxes, polyethylene waxes, ester waxes, fatty acids and other waxy materials, fatty amide containing materials, sulfonamide materials, resinous materials made from different natural sources (tall oil rosins and rosin esters, for example), and many synthetic resins, oligomers, polymers, and copolymers.
U.S. Pat. No. 6,576,747 (Carlini et al.), the disclosure of which is totally incorporated herein by reference, discloses a process for preparing dianthranilate compounds which comprises (a) admixing reactants as follows: (1) a diol of the formula R1(OH)2, wherein R1 is an alkylene group having at least about 20 carbon atoms, and wherein the —OH groups are primary or secondary, (2) isatoic anhydride, present in an amount of at least about 2 moles of isatoic anhydride per every one mole of diol, (3) a catalyst which is 1,4-diazabicyclo(2.2.2)octane, N,N,N′,N′-tetramethylethylene diamine, or a mixture thereof, said catalyst being present in an amount of at least about 0.2 mole of catalyst per every one mole of diol, and (4) a solvent; and (b) heating the mixture thus formed to form a dianthranilate compound of the formula
Also disclosed is a process for preparing diazopyridone colorants which comprises (I) preparing a dianthranilate compound by the aforementioned method, (II) reacting the dianthranilate compound with nitrosylsulfuric acid to form a diazonium salt, and (III) reacting the diazonium salt with a pyridone compound to form a diazopyridone compound.
U.S. Pat. No. 6,713,614 (Carlini et al.), the disclosure of which is totally incorporated herein by reference, discloses compounds of the formula
The compounds are useful as colorants, particularly in applications such as phase change inks.
U.S. Pat. No. 6,663,703 (Wu et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula

U.S. Pat. No. 6,755,902 (Banning et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula

U.S. Pat. No. 6,590,082 (Banning et al.), the disclosure of which is totally incorporated herein by reference, discloses compounds of the formula
The compounds are useful as colorants, particularly in applications such as phase change inks.
U.S. Pat. No. 6,696,552 (Mayo et al.), the disclosure of which is totally incorporated herein by reference, discloses a process for preparing substituted pyridone compounds which comprises (a) admixing in the absence of a solvent (1) an amine of the formula R1—NH2 wherein R1 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and (2) a first ester of the formula
wherein R2 is an electron withdrawing group and R3 is an alkyl group; (b) heating the mixture containing the amine and the first ester to form an intermediate compound of the formula
(c) admixing the intermediate compound with (1) a base and (2) a second ester of the formula
wherein R4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group and R5 is an alkyl group, said second ester being present in a molar excess relative to the intermediate compound, said base being present in a molar excess relative to the intermediate compound, and (d) heating the mixture containing the intermediate compound, the second ester, and the base to form a pyridone compound of the formula
or a salt thereof. Also disclosed is a process for preparing diazopyridone colorants which comprises preparing a pyridone compound by the above process and reacting the pyridone compound with a diazonium salt to form a diazopyridone compound.
U.S. Pat. No. 6,576,748 (Carlini et al.), the disclosure of which is totally incorporated herein by reference, discloses a process for preparing a diazopyridone compound which comprises (a) preparing a first solution comprising (1) either (A) a dianiline of the formula
or (B) an aniline of the formula
and (2) a first solvent mixture comprising (I) a solvent, (II) acetic acid, and (III) an optional second acid, said acetic acid being present in the solvent mixture in an amount of at least about 95 percent by weight of the solvent mixture, said first solution being at a temperature of about +15° C. or lower; (b) adding to the first solution nitrosylsulfuric acid, thereby forming a diazonium salt either (A) of the formula
or (B) of the formula
(c) preparing a second solution comprising (1) a second solvent mixture comprising water and an organic solvent soluble in or miscible in water, (2) either (A) a pyridone of the formula
or (B) a dipyridone of the formula
(3) a base present in an amount of at least about 3 molar equivalents of base per mole of pyridone moiety, and (4) an optional buffer salt, and (d) combining either (A) the second solution containing the dianiline and the first solution containing the pyridone, or (B) the second solution containing the aniline and the first solution containing the dipyridone to form a third solution and effect a coupling reaction to form a diazopyridone compound either (A) of the formula
or (B) of the formula

U.S. Pat. No. 6,646,111 (Carlini et al.), the disclosure of which is totally incorporated herein by reference, discloses compounds of the formula
The compounds are useful as colorants, particularly in applications such as phase change inks.
U.S. Pat. No. 6,673,139 (Wu et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula

European Patent Publication 1 125 990 A1 and PCT Patent Publication WO 01/09256 A1, the disclosures of each of which are totally incorporated herein by reference, discloses an aqueous ink for ink jet recording which contains at least a water-insoluble coloring matter, water, and a resin as main components and which takes the form of an emulsion, which is characterized by containing at least one yellow hue coloring matter selected from the group consisting of a quinophthalone compound represented by the formula (1)
wherein each of R1 to R3 independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, —CONR4R5, or —COOR6 (in which each of R4 to R6 independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group) and all of R1 to R3 are not a hydrogen atom at the same time, and a pyridone azo compound represented by the formula (2)
wherein each of R7 to R11 independently represents a hydrogen atom, a halogen atom, an unsubstituted or substituted alkyl group, an aralkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a hydroxyl group, —NR14R15 (in which R14 and R15 independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, or an aralkyl group), —COX1 (in which X1 represents an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryloxy group, or —NR16R17 (in which each of R16 and R17 independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an aralkyl group, or an unsubstituted or substituted aryl group)), —COO(CH2)n—COX2, —OCOX3, or —NHCOX4 (in which each of X2 to X4 independently represents an unsubstituted or substituted alkyl group, an aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted alkoxy group, or an unsubstituted or substituted aryloxy group, and n is an integer of 1 to 3), R12 represents an unsubstituted or substituted alkyl group, and R13 represents an unsubstituted or substituted alkyl group, an aralkyl group, or an unsubstituted or substituted aryl group. The ink is for ink jet recording having excellent light resistance and storage stability, and enables formation of a high quality image without blotting, and the obtained recording image is excellent in water resistance.
PCT Patent Publication WO 01/21714, the disclosure of which is totally incorporated herein by reference, discloses compositions comprising a solvent and at least one compound of the formula
in which R1 represents H, an optionally substituted C1-8 carbyl derived group, or a group of the formula
where C is from 2 to 6, R3 represents optionally substituted C1-8 carbyl derived group, R4 and R5 independently represent an optional substituent, R2 represents an optionally substituted C1-8 carbyl derived group, X, Y, and Z independently represent H or an optional substituent, M represents H or a cation, and m and n independently represent 0, 1, or 2. Also disclosed are compounds of the above formula providing that at least one of R1, R2, X, Y, or Z comprises a group of formula SO3M or PO3M2. These compositions and compounds are useful as the colorants to prepare color filters for displays.
U.S. Pat. No. 4,247,456 (von Brachel et al.), the disclosure of which is totally incorporated herein by reference, discloses water-insoluble monoazo dyes of the formula
wherein R is the residue of a benzene, naphthalene, diphenyl, diphenylmethane, or heterocyclic diazo compound which is free from water solubilizing groups, produced by reacting a diazotized amine of the benzene, naphthalene, diphenyl, diphenylmethane, or heterocyclic series which is free from water solubilizing groups with the appropriate 6-hydroxy-2-pyridone and the utility thereof for the dyeing and printing of synthetic fabric materials to yellow to red shades having excellent fastness to light and sublimation.
U.S. Pat. No. 3,957,749 (von Brachel et al.), the disclosure of which is totally incorporated herein by reference, discloses water-insoluble monoazo dyes of the formula
produced by reacting a diazotized amine of the benzene, naphthalene, diphenyl, diphenylmethane, or heterocyclic series which is free from water solubilizing groups with the appropriate 6-hydroxy-2-pyridone and the utility thereof for the dyeing and printing of synthetic fabric materials to yellow to red shades having excellent fastness to light and sublimation.
Japanese Patent Publication JP 05331382, the disclosure of which is totally incorporated herein by reference, discloses a specific pyridone azo pigment which is bright yellow and highly soluble in a solvent, absorbs light of long wavelength, and is useful for a thermal transfer sheet. The pyridone azo pigment is represented by the formula
wherein R is H, alkyl, substituted alkyl, cycloalkyl, aryl, or optionally substituted phenyl, and ring A is a benzene ring optionally having a nonionic group. The pigment is prepared by diazotizing an aniline compound and coupling the resulting diazo compound with a pyridone compound. Having a good solubility in an organic solvent and a good dispersibility in water, the pigment facilitates the preparation of an ink containing a high concentration of the pigment homogeneously dissolved or dispersed. The prepared ink enables the preparation of a thermal transfer sheet coated with the ink uniformly in a high density.
British Patent 1,559,001 (Harvey et al.), the disclosure of which is totally incorporated herein by reference, discloses a hydrophilic textile material colored with a dyestuff of the formula
wherein D is the residue of a diazo or tetrazo component; R1 is a hydrogen atom or an alkyl, chloro, acetamido, benzamido, carbamoyl, or an N-substituted carbamyl, for example —CONHBr, group or, preferably, a cyano group; R2 is an alkyl group, especially methyl, optionally substituted with a chlorine atom, a phenyl group, optionally substituted with an alkyl or alkoxy group, or a carboxylic acid or carboxylic acid ester group; or R1 and R2 together with the carbon atoms in the 3- or 4-position of the pyridone ring may form an alicyclic or aromatic ring system so that, for example, R1 and R2 together may be a tri- or tetra-methylene group forming with the pyridone of penteno (c) or hexeno (c) pyrid-2-one, or R1 and R2 may form together with the adjacent carbon atoms of the pyridone ring a benzene ring giving a benz (c) pyrid-2-one; R3 is an aryl group carrying one or more substituents selected from —NO, —SO2R1, —COR1, —COOR1, —CF, or —CN, wherein R1 is an optionally substituted alkyl or aryl group; and n is an integer which may be 1 or 2.
German Patent Publication DE 19646430, the disclosure of which is totally incorporated herein by reference, discloses dye mixtures comprising at least two structurally different dyes, each corresponding to formula
wherein R1 is C1-C4 alkyl; R2 is the (CH2)nO—R5 radical; R5 is, independently of R1, C1-C4 alkyl or phenyl (which is unsubstituted or substituted by C1-C4 alkyl, C1-C4 alkoxy, hydroxy, or halogen); and n is 2 or 3, which dye mixtures are suitable for dyeing or printing textile fibre materials (e.g. polyester materials), giving dyeings having good around fastness properties.
German Patent Publication DE 19646429, the disclosure of which is totally incorporated herein by reference, discloses dye mixtures comprising at least two structurally different dyes, each of which has the formula
in which R1 is C1-C4 alkyl and R2 is isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl; or C1-C3 alkyl which is substituted by phenyl or phenoxy; or R1 is phenyl (which is unsubstituted or substituted by C1-C4 alkyl, C1-C4 alkoxy, hydroxyl, or halogen), C1-C4 alkoxy-C1-C3 alkylene, phenoxy-C1-C3 alkylene, or C1-C3 alkyl which is substituted by phenyl (which is unsubstituted or substituted by C1-C4 alkyl, C1-C4 alkoxy, hydroxyl, or halogen) and R2 is C1-C10 alkyl (which is unsubstituted or substituted by hydroxyl, OCOR3, or phenoxy, where the phenyl ring in phenoxy is unsubstituted or substituted by C1-C4 alkyl, C1-C4 alkoxy, hydroxyl, or halogen) and the alkyl chain in C1-C10 alkyl from C2 can be interrupted by one or more oxygen atoms; phenyl (which is unsubstituted or substituted by C1-C4 alkyl, C1-C4 alkoxy, hydroxyl, or halogen); or C5-C7 cycloalkyl; and R3 is C1-C4 alkyl, are suitable for dyeing or printing textile fibre materials (e.g. polyester materials) and give dyeings with good allround properties.
German Patent Publication DE 19647869, the disclosure of which is totally incorporated herein by reference, discloses a dye mixture containing at least 2 dyes with different structures, each of formula
where R1 is a 1-4C alkyl; and R2 is a linear 1-3C alkyl. Also claimed is hydrophobic fibre material, preferably polyester textile material, dyed or printed with the mixture.
PCT Patent Publication WO 99/43754, the disclosure of which is totally incorporated herein by reference, discloses compounds of the formula
and salts and tautomers thereof, wherein: R1 and R2 each independently is H, optionally substituted alkyl, optionally substituted aryl, or optionally substituted arylalkyl; each W and each X independently is —COOH, —SO3H, —PO3H2, or alkyl substituted by one or more groups selected from —COOH, —SO3H, and —PO3H2; each Y and each Z independently is a substituent other than those defined for W and X; a and d each independently is 1 to 5; b and c each independently is 0 to 4; (a+b) has a value of 5 or less; and (c+d) has a value of 5 or less. Also claimed are inks containing a compound of this formula, an ink jet printing process using the inks, substrates printed with the inks, and ink jet printer cartridges containing the inks.
U.S. Pat. No. 5,929,218 (Lee et al.), the disclosure of which is totally incorporated herein by reference, discloses pyridone-based yellow monoazo dyes used in thermal transfer having following formula which have good stability and hue
wherein R1 is hydrogen atom; unsubstituted or substituted alkyl group of from 1 to 8 carbon atoms with alkoxy or aryl; or unsubstituted or substituted aryl group with alkoxy or halogen, and X is hydrogen atom; alkyl group of from 1 to 4 carbon atoms; alkoxy group; or halogen; R2 is selected from the following groups;
wherein R3 and R4 are independently selected from groups consisting hydrogen, substituted or unsubstituted alkyl group of from 1 to 4 carbon atoms, halogen, alkyl carboxylate, and carbonyl group; R3-R4 is noncyclization with R3 and R4 and selected respectively from the above substituents (R3 and R4); or saturated or unsaturated cycloalkyl of from 3 to 6 carbon atoms, Z is nitro, halogen, alkyl group of from 1 to 4 carbon atoms, alkoxy, sulfonyl, carbonyl, carboxyamide, sulfonamino, cyano, hydroxy, or hydrogen atom.
European Patent Publication EP 0 706 679 B1, U.S. Pat. No. 5,853,929 (Campbell), and PCT Patent Publication WO 95/00885, the disclosures of each of which are totally incorporated herein by reference, disclose colored cyan toner for electroreprography and laser printing based on Solvent Blue 70, and a trichomatic set of coloured toners based on Solvent Blue 70, benzodifuranone red dyes, and azo pyridone yellow dyes of the formula
wherein X is halogen, nitro, or a group —COOR5, R9 is C1-4 alkyl, R10 is C1-12 alkyl, R5 is C1-8 alkyl or a group of formula —(C1-3-alkylene)-(CO)q-Z wherein q is 0 or 1 and Z is —OR6 or —NR6R7 when q=1 or Z is —OR8 when q=0, R6 is selected from optionally substituted C1-8 alkyl, optionally substituted C1-8 alkoxy-C1-8 alkyl, and a second group represented by R5 in which R6 is optionally substituted C1-8 alkyl or optionally substituted C1-8 alkoxy-C1-8 alkyl, R7 is selected from H and optionally substituted C1-8 alkyl, and R8 is selected from optionally substituted C1-8 alkyl, optionally substituted C1-8 alkoxy-C1-8 alkyl, optionally substituted C1-8 alkyl sulfonyl or carbonyl, and optionally substituted phenyl sulfonyl or carbamoyl.
European Patent Publication EP 0 247 737, the disclosure of which is totally incorporated herein by reference, discloses a thermal transfer printing sheet suitable for use in a thermal transfer printing process, especially for the conversion of a digital image into a visible print, comprising a substrate having a coating comprising a dye of the formula
wherein Ring A is unsubstituted or carries, in the 2- or 4-position with respect to the azo link, at least one group selected from —CX3, X1, CN, NO2, —OCO.Y, —CO.Y, —CO.H, —OSO2.Y, and —SO2.Y, provided that A is substituted when Z is CH3 and R is C2-4-alkyl; X and X1 are each independently halogen; Y is selected from R1, —OR1, SR1, and —NR1R2; R1 is selected from C1-12-alkyl, C1-12-alkyl interrupted by one or two groups selected from —O—, —CO—, O.CO—, and —CO.O—, C3-7-cycloalkyl, mono- or bi-cyclic aryl, and C1-3-alkylene attached to an adjacent carbon atom on Ring A; R2 is selected from H, C1-12-alkyl, C3-7-cycloalkyl, and mono- or bi-cyclic aryl; Z is C1-12-alkyl or phenyl; and R is selected from C2-12-alkyl unbranched in the alpha-position, C2-12-alkyl unbranched in alpha-position and interrupted by one or two groups selected from —O—, —CO—, O.CO—, and —CO.O—, phenyl, C1-4-alkylphenyl, biphenyl, and biphenyl interrupted by a group selected from —O—, —CO—, O.CO—, and —CO.O—, each of which is free from hydrogen atoms capable of intermolecular hydrogen bonding.
U.S. Pat. No. 5,041,413 (Evans et al.), the disclosure of which is totally incorporated herein by reference, discloses a yellow dye-donor element for thermal dye transfer comprises a support having thereon a dye layer comprising a mixture of yellow dyes dispersed in a polymeric binder, at least one of the yellow dyes having the formula
wherein: each R1 independently represents a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms, a cycloalkyl group of from about 5 to about 7 carbon atoms; a substituted or unsubstituted allyl group; an aryl group of from about 6 to about 10 carbon atoms; a hetaryl group of from 5 to 10 atoms; acyl; arylsulfonyl; aminocarbonyl; aminosulfonyl; fluorosulfonyl; halogen; nitro; alkylthio; or arylthio; or any two adjacent R1's together represent the atoms necessary to form a 5- or 6-membered fused ring; n represents an integer from 0-4; R2 represents hydrogen; a substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl group as described above for R1; cyano; acyl; alkylsulfonyl; arylsulfonyl; or alkoxycarbonyl; Z represents cyano; alkoxycarbonyl; acyl; nitro; arylsulfonyl or alkylsulfonyl; Y represents hydrogen; a substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl group as described above for R1; amino; alkylamino; arylamino; acylamino; or sulfonylamino; and at least one of the other of the dyes having the formula
wherein R3 represents the same groups as R1 above; R4 and R5 each independently represents hydrogen, R3; cyano; acyloxy; alkoxy of 1 to about 6 carbon atoms; halogen; or alkoxycarbonyl; or any two of R3, R4 and R5 together represent the atoms necessary to complete a 5- to 7-membered ring; R6 represents the same groups as R3; G represents a substituted or unsubstituted alkyl, cycloalkyl or allyl group as described above for R3, NR7R8 or OR9; R7 and R8 each independently represents hydrogen, acyl or R3, with the proviso that R7 and R8 cannot both be hydrogen at the same time; or R7 and R8 together represent the atoms necessary to complete a 5- to 7-membered ring; R9 represents the same groups as R3; X represents C(R10)(R11), S, O or NR10; R10 and R11 each independently represents the same groups as R3; or R10 and R11 together represent the atoms necessary to complete a 5- to 7-membered ring; and J represents the atoms necessary to complete a 5- or 6-membered ring which may be fused to another ring system.
U.S. Pat. No. 4,359,418 (Lienhard et al.), the disclosure of which is totally incorporated herein by reference, discloses azo dyestuff sulfonic acid salts of the formula
wherein A represents a carbocyclic or heterocyclic aromatic radical, B represents an aliphatic, cycloaliphatic or araliphatic amine, X represents a hydrogen atom or a substituted or unsubstituted alkyl group, a cycloalkyl, aralkyl or aryl group, Y represents a hydrogen or halogen atom, a nitro, cyano, acyl, sulfonic acid, arylsulfonyl, alkoxycarbonyl group or a substituted or unsubstituted alkyl, sulfamoyl or carbamoyl group, Z represents a substituted or unsubstituted alkyl group or an aryl radical, m and n are 1 or 2; said dyestuffs salts having good solubility in organic solvents and functioning to color solutions of film forming polymers in yellow to orange shades.
German Patent Publication DE 3538517 and U.S. Pat. No. 5,037,964 (Moser et al.), the disclosures of each of which are totally incorporated herein by reference, disclose sulfonic acid group-free basic azo compounds, which correspond in one of the possible tautomeric forms to the formula
their preparation and their use for dyeing paper.
Japanese Patent Publication JP 03192158, the disclosure of which is totally incorporated herein by reference, discloses obtaining a yellow dye exhibiting high dyeing speed and degree of exhaustion in dyeing a textile material, leather, pulp, paper, etc., as well as excellent brightness and fastness to water by selecting a compound wherein a pyridopyridinium salt is linked to diphenylfluorene through azo groups. A cationic compound of the formula
wherein R1 is H or 1-4C alkyl; R2 is H, 1-4C alkyl, or alkoxy; and A− is an anion which has a structure wherein a tetrazo compound, of 9,9′-bis(4-anilino)fluorene is coupled with a pyridone derivative is selected as a yellow dye, which is useful for dyeing an unsized pulp or paper (e.g. a napkin, table cloth, or sanitary paper). The dyeing with the dye is carried out at a pH of 4-8, preferably 5-7, and at 10-50° C., preferably 15-30° C.
British Patent Publication GB 2 008 606, the disclosure of which is totally incorporated herein by reference, discloses water-insoluble yellow monoazo dyes suitable for dyeing hydrophobic synthetic fibres, particularly polyesters, having the formula
in which X represents OR3 or NHR3, NR3R4 (R3, R4 together optionally forming with N a ring having 5 to 6 carbon atoms), NHR5; R1 represents a hydrogen atom, an alkyl having 1 to 5 carbon atoms, (CH2)2OH or (CH2)3OR3; R2 represents CN, COOR3, CONHR3, CONR3R4 (R3, R4 together optionally forming with N a ring having 5 to 6 carbon atoms); R3 and R4 represent alkyl groups having 1 to 5 carbon atoms; and R5 represents a cycloalkyl having 5 or 6 carbon atoms. The dyes may be prepared by the reaction of
with Hal-CH2—CO—X in which Hal represents Cl or Br.
“Preparation and Evaluation of Yellow Pigments Based on H-Pyridone and Esters of Aminoterephthalic Acid,” P. Slosar et al., CHEMagazin, Vol. 9, No. 6, pp. 8-11 (1999), the disclosure of which is totally incorporated herein by reference, discloses yellow pigments based on H-pyridone and esters of aminoterephthalic acid wherein the color strength, brilliance (purity), and deepening of greenish shade were the larger the smaller alkyl is in the carbalkoxy group in o-position towards the azo group and the greater alkyl is in the carbalkoxy group in m-position towards the azo group.
Of potential background interest with respect to the present invention are the following references: U.S. Pat. Nos. 5,919,839; 5,827,918; 4,889,560; 5,372,852; “Synthesis, Morphology, and Optical Properties of Tetrahedral Oligo(phenylenevinylene) Materials,” S. Wang et al., J. Am. Chem. Soc., Vol. 120, p. 5695 (2000); “Syntheses of Amphiphilic Diblock Copolymers Containing a Conjugated Block and Their Self-Assembling Properties,” H. Wang et al., J. Am. Chem. Soc., Vol. 122, p. 6855 (2000); “Crystal Engineering of Conjugated Oligomers and the Spectral Signature of π Stacking in Conjugated Oligomers and Polymers,” A. Koren et al., Chem. Mater., Vol. 12, p. 1519 (2000); “The Chemistry of Isatoic Anhydride,” G. M. Coppola, Synthesis, p. 505 (1980); “Isatoic Anhydride. IV. Reactions with Various Nucleophiles,” R. P. Staiger et al., J. Org. 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While known compositions and processes are suitable for their intended purposes, a need remains for new yellow colorant compositions. In addition, a need remains for yellow colorant compositions particularly suitable for use in phase change inks. Further, a need remains for yellow colorants with desirable thermal stability. Additionally, a need remains for yellow colorants that exhibit minimal undesirable discoloration when exposed to elevated temperatures. There is also a need for yellow colorants that exhibit a desirable brilliance. In addition, there is a need for yellow colorants that exhibit a desirable hue. Further, there is a need for yellow colorants that are of desirable chroma. Additionally, there is a need for yellow colorants that have desirably high lighffastness characteristics. A need also remains for yellow colorants that have a desirably pleasing color. In addition, a need remains for yellow colorants that exhibit desirable solubility characteristics in phase change ink carrier compositions. Further, a need remains for yellow colorants that enable phase change inks to be jetted at temperatures of over 135° C. while maintaining thermal stability. Additionally, a need remains for yellow colorants that enable phase change inks that generate images with low pile height. There is also a need for yellow colorants that enable phase change inks that generate images that approach lithographic thin image quality. In addition, there is a need for yellow colorants that exhibit oxidative stability. Further, there is a need for yellow colorants that do not precipitate from phase change ink carriers. Additionally, there is a need for yellow colorants that do not, when included in phase change inks, diffuse into adjacently printed inks of different colors. A need also remains for yellow colorants that do not leach from media such as phase change ink carriers into tape adhesives, paper, or the like. In addition, a need remains for yellow colorants that, when incorporated into phase change inks, do not lead to clogging of a phase change ink jet printhead. Further, there is a need for yellow colorants that enable phase change inks that generate images with sharp edges that remain sharp over time. Additionally, there is a need for yellow colorants that enable phase change inks that generate images which retain their high image quality in warm climates. Further, there is a need for yellow colorants that enable phase change inks that generate images of desirably high optical density. Additionally, there is a need for yellow colorants that, because of their good solubility in phase change ink carriers, enable the generation of images of low pile height without the loss of desirably high optical density. A need also remains for yellow colorants that enable the use of substantially reduced amounts of colorant in, for example, an ink without decreasing the color and the spectral properties (L*a*b*) of the ink or jeopardizing the optical density or color of the prints generated with the ink. In addition, a need remains for yellow colorants that enable cost-effective inks.